Computer vision and deep learning methods have found numerous practical applications over the last decade. The field of structural health monitoring has greatly benefited from such advancements. Accurate crack detection and segmentation are a critical part of structural health monitoring and assessment. In the past decade, researchers have developed different computer vision and deep learning methods to address this challenging task. In this article, we propose to use convolutional neural networks and bootstrapping to improve crack segmentation in the wild. Specifically, we investigate fully convolutional network (FCN) and DeepLabV3 with different ResNet architectures as the back bone and assess their performance. A unique feature of this work is the use of bootstrapping with a segmentation network and image augmentation. Bootstrapping is an important component of our proposed methodology for better extracting features from the datasets. We also incorporate superpixel pooling for FCN which improves performance. We assess the performance of our method using five publicly available datasets, which include a wide variety of crack images such as thin pavement cracks, tree shadows on cracks, cracks in asphalt roads, concrete wall cracks, wide cracks on concrete surfaces, and so on. A comparative study is also performed with several established methods in the literature. Results indicate that overall, our proposed method outperforms other state‐of‐the‐art methods for crack segmentation.